Crystal structure of 4-methyl-N-{(E)-meth-yl[(3aR,8aS)-2-oxo-3,3a,8,8a-tetra-hydro-2H-indeno-[1,2-d][1,3]oxazol-3-yl]-λ(4)-sulfanyl-idene}benzene-sulfonamide.

The formulation that the title compound, C18H18N2O4S2, adopts is a zwitterionic core with the charge separated to the sulfilimine S and N atoms and is supported by the two different S-N bond distances about the sulfinimine N atom [1.594 (2) and 1.631 (2) Å, respectively] that are typical for such bonds. The notably unusual bond is S-N(oxazolidinone) [1.692 (2) Å] that is longer than a typical S-N bond [1.603 (18) Å, Mogul analysis; Macrae et al. (2008 ▸). J. Appl. Cryst. 41, 466-470]. The bond-angle sum about sulfilimine sulfur (308.35°) reflects the trigonal-pyramidal geometry of this atom. Two of the angles are less than 100°. Despite the pyramidalization of this sulfur, there are no significant inter-molecular inter-actions, beyond usual van der Waals contacts, in the crystal packing.

Related literature

Oxazolidinone sulfilimines are synthesized as precursors of vinyl sulfilimines which are used in the γ-lactamization reaction to generate chiral pyrrolidinones with medicinal chemistry inter­est. For the synthesis, see: Celentano & Colonna (1998 ▸); Silveira & Marino (2013 ▸). For sulfonyl oxazolidinone structures, see: Barbey et al. (2012 ▸); Berredjem et al. (2010 ▸); Bonnaud et al. (1987 ▸); Dewynter et al. (1997 ▸). For related vinyl sulfonamide chemistry, see: Silveira et al. (2013 ▸). For related oxazolidinone sulfinime structures, see: Silveira et al. (2012 ▸, 2014 ▸). For the Hooft parameter, see: Hooft et al. (2008 ▸).

Experimental

Crystal data

C18H18N2O4S2

M = 390.46

Orthorhombic,

a = 6.8841 (1) Å

b = 12.2326 (2) Å

c = 20.1911 (4) Å

V = 1700.30 (5) Å3

Z = 4

Cu Kα radiation

μ = 3.09 mm−1

T = 100 K

0.42 × 0.40 × 0.34 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Krause et al., 2015 ▸) T min = 0.701, T max = 0.929

11963 measured reflections

3004 independent reflections

2984 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.028

wR(F 2) = 0.070

S = 1.11

3004 reflections

237 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.36 e Å−3

Absolute structure: Flack x determined using 1183 quotients [(I +)−(I −)]/[(I +)+(I −)] (Parsons et al., 2013 ▸)

Absolute structure parameter: 0.052 (4)

Data collection: APEX2 (Bruker, 2007 ▸); cell refinement: APEX2 and SAINT (Bruker, 2007 ▸); data reduction: SAINT and XPREP (Bruker, 2007 ▸); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015 ▸); molecular graphics: XP in SHELXTL (Sheldrick, 2008 ▸); software used to prepare material for publication: XCIF (Sheldrick, 2008 ▸) and publCIF (Westrip, 2010 ▸).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S2056989015024779/nk2234sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015024779/nk2234Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015024779/nk2234Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015024779/nk2234fig1.tif

Labeling diagram of the title compound. Atomic displacement ellipsoids depicted at the 50% probability level. Hydrogen atoms depicted as spheres of an arbitrary radius.

CCDC reference: 1444186

Additional supporting information: crystallographic information; 3D view; checkCIF report

C18H18N2O4S2	Dx = 1.525 Mg m−3
Mr = 390.46	Cu Kα radiation, λ = 1.54178 Å
Orthorhombic, P212121	Cell parameters from 9988 reflections
a = 6.8841 (1) Å	θ = 4.2–69.2°
b = 12.2326 (2) Å	µ = 3.09 mm−1
c = 20.1911 (4) Å	T = 100 K
V = 1700.30 (5) Å3	Parallelepiped, clear colorless
Z = 4	0.42 × 0.40 × 0.34 mm
F(000) = 816

Bruker SMART APEX CCD diffractometer	3004 independent reflections
Radiation source: fine-focus sealed tube, Siemens KFFCU2K-90	2984 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
Detector resolution: 8.33 pixels mm-1	θmax = 69.5°, θmin = 4.2°
φ and ω scans	h = −8→8
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	k = −14→14
Tmin = 0.701, Tmax = 0.929	l = −24→22
11963 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.028	H-atom parameters constrained
wR(F2) = 0.070	w = 1/[σ2(Fo2) + (0.0405P)2 + 0.5066P] where P = (Fo2 + 2Fc2)/3
S = 1.11	(Δ/σ)max = 0.001
3004 reflections	Δρmax = 0.29 e Å−3
237 parameters	Δρmin = −0.36 e Å−3
0 restraints	Absolute structure: Flack x determined using 1183 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.052 (4)

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

	x	y	z	Uiso*/Ueq
S1	0.45871 (9)	0.55630 (5)	0.77781 (3)	0.00978 (15)
S2	0.67201 (9)	0.69687 (5)	0.85264 (3)	0.01185 (16)
O1	0.3825 (3)	0.25928 (14)	0.82183 (9)	0.0148 (4)
O2	0.6694 (3)	0.34297 (15)	0.80444 (9)	0.0176 (4)
O3	0.8276 (3)	0.63677 (15)	0.82056 (9)	0.0175 (4)
O4	0.6751 (3)	0.81443 (15)	0.84687 (9)	0.0185 (4)
N1	0.3831 (3)	0.44084 (18)	0.81606 (11)	0.0127 (5)
N2	0.4579 (3)	0.65675 (17)	0.82812 (11)	0.0132 (5)
C1	0.4975 (4)	0.3476 (2)	0.81239 (12)	0.0129 (5)
C2	0.1767 (4)	0.2920 (2)	0.82310 (13)	0.0136 (5)
H2	0.1106	0.2809	0.7795	0.016*
C3	0.0725 (4)	0.2347 (2)	0.87983 (13)	0.0148 (6)
H3A	−0.0688	0.2299	0.8713	0.018*
H3B	0.1246	0.1601	0.8867	0.018*
C4	0.1142 (4)	0.3068 (2)	0.93859 (13)	0.0124 (5)
C5	0.0916 (4)	0.2842 (2)	1.00541 (13)	0.0140 (6)
H5	0.0423	0.2157	1.0198	0.017*
C6	0.1431 (4)	0.3648 (2)	1.05088 (13)	0.0161 (6)
H6	0.1258	0.3512	1.0968	0.019*
C7	0.2188 (4)	0.4644 (2)	1.03076 (14)	0.0157 (6)
H7	0.2569	0.5170	1.0628	0.019*
C8	0.2393 (4)	0.4875 (2)	0.96324 (14)	0.0141 (5)
H8	0.2899	0.5558	0.9488	0.017*
C9	0.1843 (4)	0.4088 (2)	0.91814 (13)	0.0117 (5)
C10	0.1900 (4)	0.41298 (19)	0.84277 (13)	0.0116 (5)
H10	0.0833	0.4584	0.8234	0.014*
C11	0.2421 (4)	0.5860 (2)	0.73290 (13)	0.0149 (6)
H11A	0.1358	0.5997	0.7641	0.022*
H11B	0.2089	0.5237	0.7046	0.022*
H11C	0.2627	0.6510	0.7054	0.022*
C12	0.6749 (4)	0.6636 (2)	0.93784 (12)	0.0112 (5)
C13	0.6177 (4)	0.7407 (2)	0.98430 (13)	0.0136 (5)
H13	0.5750	0.8110	0.9706	0.016*
C14	0.6237 (4)	0.7138 (2)	1.05134 (13)	0.0153 (6)
H14	0.5858	0.7664	1.0834	0.018*
C15	0.6846 (4)	0.6107 (2)	1.07178 (13)	0.0157 (5)
C16	0.7366 (4)	0.5341 (2)	1.02403 (14)	0.0152 (6)
H16	0.7745	0.4628	1.0376	0.018*
C17	0.7344 (4)	0.5596 (2)	0.95710 (14)	0.0147 (5)
H17	0.7727	0.5071	0.9250	0.018*
C18	0.6940 (5)	0.5854 (2)	1.14496 (14)	0.0231 (6)
H18A	0.7504	0.5126	1.1514	0.035*
H18B	0.5628	0.5871	1.1637	0.035*
H18C	0.7752	0.6400	1.1672	0.035*

	U11	U22	U33	U12	U13	U23
S1	0.0116 (3)	0.0111 (3)	0.0066 (3)	−0.0007 (2)	0.0007 (2)	0.0007 (2)
S2	0.0124 (3)	0.0139 (3)	0.0093 (3)	−0.0022 (2)	0.0002 (2)	−0.0003 (2)
O1	0.0189 (10)	0.0105 (8)	0.0151 (9)	0.0019 (7)	0.0014 (7)	−0.0003 (7)
O2	0.0161 (9)	0.0186 (9)	0.0179 (9)	0.0046 (8)	0.0011 (8)	0.0004 (8)
O3	0.0116 (9)	0.0269 (10)	0.0140 (9)	−0.0032 (8)	0.0015 (8)	−0.0017 (8)
O4	0.0251 (10)	0.0161 (9)	0.0143 (9)	−0.0067 (8)	−0.0028 (8)	0.0036 (7)
N1	0.0141 (11)	0.0108 (10)	0.0133 (10)	0.0016 (9)	0.0039 (9)	0.0032 (9)
N2	0.0135 (11)	0.0141 (10)	0.0118 (10)	0.0004 (9)	0.0001 (9)	−0.0013 (9)
C1	0.0170 (14)	0.0137 (12)	0.0080 (12)	0.0023 (10)	0.0010 (10)	−0.0015 (10)
C2	0.0157 (13)	0.0129 (12)	0.0121 (12)	−0.0016 (11)	−0.0025 (11)	0.0014 (10)
C3	0.0173 (14)	0.0137 (12)	0.0134 (13)	−0.0036 (10)	−0.0014 (11)	0.0008 (11)
C4	0.0116 (11)	0.0133 (12)	0.0121 (12)	0.0020 (10)	−0.0014 (10)	0.0006 (11)
C5	0.0109 (12)	0.0164 (13)	0.0149 (13)	0.0002 (10)	0.0010 (10)	0.0059 (10)
C6	0.0122 (13)	0.0256 (14)	0.0106 (12)	0.0041 (11)	0.0015 (10)	0.0017 (11)
C7	0.0107 (13)	0.0218 (13)	0.0145 (13)	0.0024 (10)	−0.0001 (10)	−0.0054 (11)
C8	0.0114 (12)	0.0135 (12)	0.0174 (13)	0.0023 (10)	0.0033 (10)	−0.0010 (11)
C9	0.0090 (11)	0.0148 (12)	0.0111 (12)	0.0030 (10)	0.0025 (11)	0.0023 (10)
C10	0.0112 (12)	0.0120 (12)	0.0117 (12)	0.0003 (9)	0.0010 (11)	0.0030 (9)
C11	0.0168 (13)	0.0158 (12)	0.0122 (13)	−0.0026 (10)	−0.0057 (10)	0.0050 (10)
C12	0.0087 (11)	0.0168 (12)	0.0080 (11)	−0.0023 (10)	−0.0023 (10)	0.0024 (9)
C13	0.0106 (12)	0.0158 (12)	0.0142 (13)	−0.0013 (10)	−0.0004 (10)	0.0011 (11)
C14	0.0116 (12)	0.0215 (13)	0.0127 (12)	−0.0028 (10)	0.0013 (10)	−0.0013 (10)
C15	0.0111 (12)	0.0223 (13)	0.0136 (13)	−0.0054 (11)	−0.0024 (11)	0.0031 (11)
C16	0.0107 (12)	0.0156 (12)	0.0192 (13)	−0.0008 (10)	−0.0024 (10)	0.0050 (11)
C17	0.0103 (12)	0.0158 (12)	0.0180 (13)	−0.0003 (10)	0.0015 (10)	−0.0028 (11)
C18	0.0263 (16)	0.0287 (15)	0.0144 (13)	−0.0091 (12)	−0.0016 (13)	0.0049 (11)

S1—N2	1.594 (2)	C7—C8	1.399 (4)
S1—N1	1.692 (2)	C7—H7	0.9500
S1—C11	1.782 (3)	C8—C9	1.378 (4)
S2—O4	1.4430 (19)	C8—H8	0.9500
S2—O3	1.451 (2)	C9—C10	1.523 (3)
S2—N2	1.631 (2)	C10—H10	1.0000
S2—C12	1.768 (2)	C11—H11A	0.9800
O1—C1	1.353 (3)	C11—H11B	0.9800
O1—C2	1.472 (3)	C11—H11C	0.9800
O2—C1	1.195 (3)	C12—C13	1.387 (4)
N1—C1	1.388 (3)	C12—C17	1.392 (4)
N1—C10	1.475 (3)	C13—C14	1.394 (4)
C2—C3	1.522 (4)	C13—H13	0.9500
C2—C10	1.535 (3)	C14—C15	1.391 (4)
C2—H2	1.0000	C14—H14	0.9500
C3—C4	1.506 (4)	C15—C16	1.392 (4)
C3—H3A	0.9900	C15—C18	1.511 (4)
C3—H3B	0.9900	C16—C17	1.387 (4)
C4—C5	1.386 (4)	C16—H16	0.9500
C4—C9	1.400 (4)	C17—H17	0.9500
C5—C6	1.393 (4)	C18—H18A	0.9800
C5—H5	0.9500	C18—H18B	0.9800
C6—C7	1.386 (4)	C18—H18C	0.9800
C6—H6	0.9500
N2—S1—N1	110.58 (11)	C9—C8—H8	120.8
N2—S1—C11	99.43 (12)	C7—C8—H8	120.8
N1—S1—C11	98.34 (11)	C8—C9—C4	121.5 (2)
O4—S2—O3	117.24 (12)	C8—C9—C10	129.0 (2)
O4—S2—N2	106.79 (12)	C4—C9—C10	109.5 (2)
O3—S2—N2	112.27 (11)	N1—C10—C9	113.4 (2)
O4—S2—C12	107.93 (11)	N1—C10—C2	100.5 (2)
O3—S2—C12	108.03 (12)	C9—C10—C2	103.0 (2)
N2—S2—C12	103.67 (12)	N1—C10—H10	113.0
C1—O1—C2	110.39 (19)	C9—C10—H10	113.0
C1—N1—C10	110.0 (2)	C2—C10—H10	113.0
C1—N1—S1	119.14 (18)	S1—C11—H11A	109.5
C10—N1—S1	129.59 (17)	S1—C11—H11B	109.5
S1—N2—S2	114.97 (13)	H11A—C11—H11B	109.5
O2—C1—O1	124.1 (2)	S1—C11—H11C	109.5
O2—C1—N1	127.5 (2)	H11A—C11—H11C	109.5
O1—C1—N1	108.5 (2)	H11B—C11—H11C	109.5
O1—C2—C3	110.0 (2)	C13—C12—C17	121.0 (2)
O1—C2—C10	102.1 (2)	C13—C12—S2	119.9 (2)
C3—C2—C10	106.1 (2)	C17—C12—S2	119.0 (2)
O1—C2—H2	112.7	C12—C13—C14	119.2 (2)
C3—C2—H2	112.7	C12—C13—H13	120.4
C10—C2—H2	112.7	C14—C13—H13	120.4
C4—C3—C2	103.5 (2)	C15—C14—C13	120.7 (3)
C4—C3—H3A	111.1	C15—C14—H14	119.6
C2—C3—H3A	111.1	C13—C14—H14	119.6
C4—C3—H3B	111.1	C14—C15—C16	118.9 (2)
C2—C3—H3B	111.1	C14—C15—C18	119.3 (3)
H3A—C3—H3B	109.0	C16—C15—C18	121.9 (3)
C5—C4—C9	120.2 (2)	C17—C16—C15	121.3 (2)
C5—C4—C3	128.9 (2)	C17—C16—H16	119.3
C9—C4—C3	110.8 (2)	C15—C16—H16	119.3
C4—C5—C6	118.1 (2)	C16—C17—C12	118.8 (2)
C4—C5—H5	120.9	C16—C17—H17	120.6
C6—C5—H5	120.9	C12—C17—H17	120.6
C7—C6—C5	121.6 (2)	C15—C18—H18A	109.5
C7—C6—H6	119.2	C15—C18—H18B	109.5
C5—C6—H6	119.2	H18A—C18—H18B	109.5
C6—C7—C8	120.1 (3)	C15—C18—H18C	109.5
C6—C7—H7	120.0	H18A—C18—H18C	109.5
C8—C7—H7	120.0	H18B—C18—H18C	109.5
C9—C8—C7	118.3 (2)

S1—N2	1.594 (2)
S1—N1	1.692 (2)
S1—C11	1.782 (3)
S2—O4	1.4430 (19)
S2—O3	1.451 (2)
S2—N2	1.631 (2)
S2—C12	1.768 (2)

N2—S1—N1	110.58 (11)
N2—S1—C11	99.43 (12)
N1—S1—C11	98.34 (11)
O4—S2—O3	117.24 (12)
O4—S2—N2	106.79 (12)
O3—S2—N2	112.27 (11)
O4—S2—C12	107.93 (11)
O3—S2—C12	108.03 (12)
N2—S2—C12	103.67 (12)